Buying Legal Tech Isn't a Check-the-Box Exercise

I've spent years watching teams roll out legal tech, and the same mistake keeps coming up. The new tool gets treated as the fix for everything that's broken. It almost never works out that way.

We've all got parts of our day that could be smoother, faster, or just less painful. So, when procurement time rolls around, technology starts to look like the finish line. “If only we had this, everything would be better.” I call it the halo effect. It's the quiet belief that the tool itself is the answer. Nothing has made this more obvious than with the advent of AI and its proliferation into legal tech solutions. Everyone wants it and everyone's convinced they need it but far fewer people have stopped to ask where AI will actually improve the work they do today.

The best legal tech procurement I've seen always starts well before anyone attends a vendor demo for a particular solution. Rather than papering over a bad process with AI or any other technology, clients who want real result often turn to some honest, unglamorous homework first.

These teams often sit down and work through five important questions: (1) What can be done better; (2) What can genuinely be improved by technology; (3) which technology is right for the job; (4) how the process should be reshaped first, and; (5) whether the improvement will actually be adopted?

Let’s break down each one:

1. What Can Be Done Better?

Audit what your team actually does day to day and pull out the use cases that are crying out for improvement. Sort them into low and high impact, then go after the high-impact ones first. Matter intake is a good example. Plenty of in-house teams don't have a real intake process. Work turns up as emails to a shared inbox that lawyers grab on a first-cab-off-the-rank basis, or as messages landing in someone's Teams or Slack. That's a high-value candidate for a rethink.

2. What Can Be Improved By Technology?

Not every problem needs a tech solution, and even when it does, not every tool is the right one (more on that next). Be honest about whether technology genuinely helps here, or whether you’re, for example, reaching for software to solve something a conversation could fix. Take the monthly report that takes someone a full day to pull together and that almost nobody reads. Before you rush to automate it, the better question is whether it needs to exist at all. Sometimes the fix is a better habit, not a better tool. The trick is knowing which is which before you spend a cent.

3. The Right Technology to Embed the Improvement

Not all tools are created equal, and the one everyone’s talking about isn’t automatically the right one for your job. We dug into this in our last post, Different Problems Need Different Legal AI Tools. Here's How to Tell the Difference. The short version is that legal work isn’t one problem, so it can’t have one answer. Match the tool to the shape of the problem, not to the noise around it.

4. How the Process Should Be Reshaped Before You Adopt Anything

This might be the most important point on the list, and it’s where most teams come unstuck. Before you bring in anything new, sit with your current process and be honest about how you really work and where it could be streamlined. Workflow digitization is the classic trap. When teams move a manual workflow into a digital system, they tend to recreate exactly what they did before. Same steps, same hand-offs, just on a screen now. That almost never produces the best result. New technology should be a reset. It’s a chance to audit, rethink, and rebuild the process so it actually benefits from the tool and is better to use. Yes, that means upfront work like policy changes, stakeholder management and client feedback sessions. But it pays off. Too often we see teams adopt first and discover the gaps during rollout, by which point the pressure to ship has taken over and the result suffers for it.

5. Whether the Improvement Will Actually Be Adopted

We all have lofty ideas about the tools we choose, but in the end real people have to use them, and those people may have zero interest in the shiny thing you’ve handed them. Get buy-in early. Run roadshows, test the appetite for change, find out what your team actually wants. Sometimes change is non-negotiable and people simply have to adjust, but even then, it’s good change management that turns a mandate into genuine adoption. Work this out before you buy, not after. And be honest with yourself and your vendor. You can buy the Ferrari or the Rolls Royce of products, but if your driver’s a jockey, the ROI simply isn’t going to be there.

Key Takeaways

Over the years, I’ve seen what the right tool dropped into the right process can do and conversely what the right tool in the wrong process cannot. The technology you end up choosing is rarely the hard part, it’s the work that precedes the choice that ultimately makes or breaks the implementation. If you do that pre-work honestly, ask the hard questions, be prepared to hit reset on certain ways of working, and drive adoption then the tool you choose will be put in the best place to achieve the desired efficiency gains. Check-the-box procurement might get you a tool that works, but it takes everything before the box gets ticked to get a tool that delivers.

Here at Checkbox, we believe the right technology should facilitate a great process, not stand in for one. A well-thought-out process deserves a platform that can actually deliver it, and that’s exactly what we’ve built. Do the thinking, shape the process around how your team really works, and Checkbox is what puts it into motion, turning a well-designed process into results you can count on time after time.